Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety

Identification of the novel (E)-N′-((2-chloro-7-methoxyquinolin-3-yl)methylene)-3-(phenylthio)propanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19–26 were prepared from the correspo...

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Main Authors:	Murat Bingul, Owen Tan, Christopher R. Gardner, Selina K. Sutton, Greg M. Arndt, Glenn M. Marshall, Belamy B. Cheung, Naresh Kumar, David StC. Black
Format:	Article
Language:	English
Published:	MDPI AG 2016-07-01
Series:	Molecules
Subjects:	quinoline hydrazide-hydrazone anticancer neuroblastoma breast cancer
Online Access:	http://www.mdpi.com/1420-3049/21/7/916

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spelling	doaj-333f7a73b761430e8ecd8b6a2dc991e62020-11-25T00:05:17ZengMDPI AGMolecules1420-30492016-07-0121791610.3390/molecules21070916molecules21070916Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline MoietyMurat Bingul0Owen Tan1Christopher R. Gardner2Selina K. Sutton3Greg M. Arndt4Glenn M. Marshall5Belamy B. Cheung6Naresh Kumar7David StC. Black8School of Chemistry, The University of New South Wales Australia, Sydney, NSW 2052, AustraliaChildren’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales Australia, Sydney, NSW 2031, AustraliaSchool of Chemistry, The University of New South Wales Australia, Sydney, NSW 2052, AustraliaChildren’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales Australia, Sydney, NSW 2031, AustraliaChildren’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales Australia, Sydney, NSW 2031, AustraliaChildren’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales Australia, Sydney, NSW 2031, AustraliaChildren’s Cancer Institute Australia for Medical Research, Lowy Cancer Research Centre, The University of New South Wales Australia, Sydney, NSW 2031, AustraliaSchool of Chemistry, The University of New South Wales Australia, Sydney, NSW 2052, AustraliaSchool of Chemistry, The University of New South Wales Australia, Sydney, NSW 2052, AustraliaIdentification of the novel (E)-N′-((2-chloro-7-methoxyquinolin-3-yl)methylene)-3-(phenylthio)propanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19–26 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using EDC-mediated peptide coupling reactions. Further modification of the parent compound 18 was achieved by replacement of the quinoline moiety with other aromatic systems. All the newly synthesized compounds were evaluated for their anti-cancer activity against the SH-SY5Y and Kelly neuroblastoma cell lines, as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Analogues 19 and 22 significantly reduced the cell viability of neuroblastoma cancer cells with micromolar potency and significant selectivity over normal cells. The quinoline hydrazide 22 also induced G1 cell cycle arrest, as well as upregulation of the p27kip1 cell cycle regulating protein.http://www.mdpi.com/1420-3049/21/7/916quinolinehydrazide-hydrazoneanticancerneuroblastomabreast cancer
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Murat Bingul Owen Tan Christopher R. Gardner Selina K. Sutton Greg M. Arndt Glenn M. Marshall Belamy B. Cheung Naresh Kumar David StC. Black
spellingShingle	Murat Bingul Owen Tan Christopher R. Gardner Selina K. Sutton Greg M. Arndt Glenn M. Marshall Belamy B. Cheung Naresh Kumar David StC. Black Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety Molecules quinoline hydrazide-hydrazone anticancer neuroblastoma breast cancer
author_facet	Murat Bingul Owen Tan Christopher R. Gardner Selina K. Sutton Greg M. Arndt Glenn M. Marshall Belamy B. Cheung Naresh Kumar David StC. Black
author_sort	Murat Bingul
title	Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety
title_short	Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety
title_full	Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety
title_fullStr	Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety
title_full_unstemmed	Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety
title_sort	synthesis, characterization and anti-cancer activity of hydrazide derivatives incorporating a quinoline moiety
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2016-07-01
description	Identification of the novel (E)-N′-((2-chloro-7-methoxyquinolin-3-yl)methylene)-3-(phenylthio)propanehydrazide scaffold 18 has led to the development of a new series of biologically active hydrazide compounds. The parent compound 18 and new quinoline derivatives 19–26 were prepared from the corresponding quinoline hydrazones and substituted carboxylic acids using EDC-mediated peptide coupling reactions. Further modification of the parent compound 18 was achieved by replacement of the quinoline moiety with other aromatic systems. All the newly synthesized compounds were evaluated for their anti-cancer activity against the SH-SY5Y and Kelly neuroblastoma cell lines, as well as the MDA-MB-231 and MCF-7 breast adenocarcinoma cell lines. Analogues 19 and 22 significantly reduced the cell viability of neuroblastoma cancer cells with micromolar potency and significant selectivity over normal cells. The quinoline hydrazide 22 also induced G1 cell cycle arrest, as well as upregulation of the p27kip1 cell cycle regulating protein.
topic	quinoline hydrazide-hydrazone anticancer neuroblastoma breast cancer
url	http://www.mdpi.com/1420-3049/21/7/916
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Synthesis, Characterization and Anti-Cancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety

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